This application is the national phase of international application PCT/JP99/03009 filed Jul. 27, 1999 which designated the U.S.
The present invention relates to novel fused heterocyclic dicarboxylic acid diamide derivatives or salts thereof, a herbicide containing said compound or salt thereof as an active ingredient, and a method for using said herbicide.
In JP-A-6-25190, there is mentioned that pyrazinedicarboxylic acid diamide derivatives are useful as herbicide. In JP-A-9-323974, there is mentioned that pyridinedicarboxylic acid diamide derivatives are useful as herbicide.
The present inventors have conducted extensive studies with the aim of developing a novel herbicide. As a result, it has been found that the fused heterocyclic dicarboxylic acid diamide derivatives represented by general formula (I) of the present invention or salts thereof are novel compounds not found in literature and having an excellent herbicidal activity. Based on this finding, the present invention has been accomplished.
The present invention relates to fused heterocyclic dicarboxylic acid diamide derivatives represented by the following general formula (I): 
wherein R1 represents hydrogen atom or (C1-C6) alkyl group;
R2 and R3 may be same or different and each represents hydrogen atom, (C1-C8) alkyl group, halo (C1-C6) alkyl group, (C3-C8) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C3-C6) cycloalkyl group having, on the ring thereof, at least one, same or different halogen atoms, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio group, alkylthio (C1-C6) alkyl group, cyano (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, amino (C1-C6) alkyl group, substituted amino (C1-C6) alkyl group substituted with one or two, same or different (C1-C6) alkyl groups, phenyl (C1-C6) alkyl group, substituted phenyl (C1-C6) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C1-C6) alkyl groups, phenyl (C1-C6) alkoxy group or substituted phenyl (C1-C6) alkoxy group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C1-C6) alkyl groups; or
R2 and R3, taken conjointly, represent a 5- to 6-membered heterocycle having at least one, same or different heteroatoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, further, the carbon atom or nitrogen atom on said heterocycle may have at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group and halo (C1-C6) alkylthio group;
X represents 0 to 5, same or different substituents selected from the group consisting of halogen atom, nitro group, cyano group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C3-C6) cycloalkyl group having, on the ring thereof, at least one, same or different halogen atoms, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkyl-sulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, amino group, substituted amino group substituted with same or different (C1-C6) alkyl groups, cyano (C1-C6) alkyl groups, phenyl (C1-C6) alkyl groups, (C1-C6) alkoxy-carbonyl (C1-C6) alkyl groups, (C1-C6) alkoxycarbonyl groups, (C1-C6) acyl groups, (C1-C6) alkylsulfonyl groups or halo (C1-C6) alkylsulfonyl groups, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, phenyl (C1-C6) alkyl group or substituted phenyl (C1-C6) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group; and 
xe2x80x83represents Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, or Q14, wherein:
Q1is a group of the following formula: 
wherein Y represents hydrogen atom, halogen atom, nitro group, cyano group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6,) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, amino group, substituted amino group having at least one, same or different substituents selected from the group consisting of (C1-C6) alkyl group, cyano (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkoxyamino-carbonyl group, (C1-C6) acyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl (C1-C6) alkyl group, (C3-C6) alkyleneimino group, hydrazino group or substituted hydrazino group substituted with same or different (C1-C6) alkyl groups; and
R4 represents 0 to 4, same or different substituents selected from the group consisting of halogen atom, nitro group, cyano group, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, methylenedioxy group, amino group and substituted amino group substituted with at least one, same or different (C1-C6) alkyl groups, cyano (C1-C6) alkyl groups, (C1-C6) alkoxycarbonyl (C1-C6) alkyl groups, (C1-C6) alkoxycarbonyl groups, (C1-C6) alkoxyaminocarbonyl groups, (C1-C6) acyl groups, (C1-C6) alkylsulfonyl groups, halo (C1-C6) alkylsulfonyl groups or phenyl (C1-C6) alkyl groups;
Q2 is a group of the following formula: 
wherein at least one of A, B, D and E represent a nitrogen atom, and the others of A, B, D and E represent Cxe2x80x94R5 wherein R5 represents hydrogen atom, halogen atom, nitro group, cyano group, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, amino group or substituted amino group having at least one, same or different substituents selected from the group consisting of (C1-C6) alkyl group, cyano (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkoxy-aminocarbonyl group, (C1-C6) acyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl (C1-C6) alkyl group; and Y is as defined above;
Q3 is a group of the following formula: 
wherein at least one of F, G, J and K represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or Nxe2x80x94R6 wherein R6 represents hydrogen atom, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkyl-sulfonyl group or halo (C1-C6) alkylsulfonyl group, and the others of F, G, J and K each represents Cxe2x80x94(R7) R8 wherein R7 and R8 may be same or different and represent hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C3-C6) cycloalkyl group having at least one, same or different halogen atoms on the ring thereof, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, phenyl (C1-C6) alkyl group, substituted phenyl (C1-C6) alkyl group substituted with at least one, same or different halogen atoms or (C1-C6) alkyl groups, amino (C1-C6) alkyl group, substituted amino (C1-C6) alkyl group substituted with at least one, same or different (C1-C6) alkyl groups or phenyl (C1-C6) alkoxy group; and Y is as defined above; and G and J may be taken conjointly to represent CHxe2x95x90CH;
Q4 is a group of the following formula: 
wherein R9 is same or different and represents halogen atom, nitro group, cyano group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group, (C1-C6) alkylthio (C1-C6) alkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, halo (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C1-C6) alkoxy group, halo (C1-C6) alkoxy group, (C1-C6) alkylthio group, halo (C1-C6) alkylthio group and phenyl group, amino group, substituted amino group substituted with at least one, same or different substituents selected from the group consisting of (C1-C6) alkyl group, cyano (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkoxyaminocarbonyl group, (C1-C6) acyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group and phenyl (C1-C6) alkyl group, (C3-C6) alkyleneimino group, hydrazino group or substituted hydrazino group substituted with same or different (C1-C6) alkyl groups; m represents an integer of 0 to 2;
Z represents oxygen atom, sulfur atom or Nxe2x80x94R10 wherein R10 represents hydrogen atom, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6) alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group or (C1-C6) alkylthio (C1-C6) alkyl group; and Y is as defined above;
Q5 is a group of the following formula: 
wherein R9, Y, Z and m are as defined above;
Q6 is a group of the following formula: 
wherein R9, Y, Z and m are as defined above;
Q7 is a group of the following formula: 
wherein at least one of L, M and T represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or Nxe2x80x94R11 wherein R11 represents hydrogen atom, hydroxyl group, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkoxycarbonyl group, (C1-C6 alkylsulfonyl group, halo (C1-C6) alkylsulfonyl group or (C1-C6) alkylthio (C1-C6) alkyl group, and the others of L, M and T each represents C-(R12)R13 wherein R12and R13 may be same or different and each represents hydrogen atom, (C1-C6) alkyl group, halo (C1-C6) alkyl group, (C3-C6) cycloalkyl group, (C3-C6) cycloalkyl (C1-C6) alkyl group, (C3-C6) cycloalkyl group having at least one, same or different halogen atoms on the ring thereof, (C1-C6) alkoxy group, (C1-C6) alkoxy (C1-C6) alkyl group, (C1-C6) alkylthio (C1-C6) alkyl group, (C1-C6) alkoxy-carbonyl (C1-C6) alkyl group, phenyl (C1-C6) alkyl group, substituted phenyl (C1-C6) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C1-C6) alkyl groups, phenyl (C1-C6) alkoxy group, substituted phenyl (C1-C6) alkoxy group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C1-C6) alkyl groups, amino (C1-C6) alkyl group or substituted amino (C1-C6) alkyl group substituted with at least one, same or different (C1-C6) alkyl groups;
Q8 is a group of the following formula: 
wherein R14 represents hydrogen atom or is the same as R9, and Y and Z are as defined above;
Q9 is a group of the following formula: 
wherein R14, Y and Z are as defined above;
Q10 is a group of the following formula: 
wherein R14, Y and Z are as defined above;
Q11 is a group of the following formula: 
wherein R14, Y and Z are as defined above;
Q12 is a group of the following formula: 
wherein R14, Y and Z are as defined above;
Q13 is a group of the following formula: 
wherein R14, Y and Z are as defined above; and
Q14 is a group of the following formula: 
wherein R9 is as defined above and n represents an integer of 0 to 4; and
salts of said compounds, a herbicide containing said compound as an active ingredient, and a method for using said herbicide.
In the definitions of the substituents in the fused heterocyclic dicarboxylic acid diamide derivatives represented by general formula (I) or salts thereof, the term xe2x80x9chalogen atomxe2x80x9d means chlorine atom, bromine atom, iodine atom or fluorine atom; the term (C1-C8) means that the number of carbon atoms is 1 to 8; the term (C1-C8) alkyl group, for example, means a straight chain or branched chain alkyl group having 1 to 8 carbon atoms; and the term xe2x80x9chalo (C1-C6) alkyl groupxe2x80x9d means a straight chain or branched chain alkyl group having 1 to 6 carbon atoms and substituted with at least one, same or different halogen atoms.
As examples of the salt, inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate and the like; organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate and the like; and salts of metal ions such as sodium ion, potassium ion, calcium ion and the like can be referred to.
As a preferable embodiment of the fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I), a case where R1 and R2 are both hydrogen atom, R3 is (C1-C6) alkyl group or (C3-C6) cycloalkyl group, X is halogen atom or (C1-C6) alkyl group, and 
is Q2, Q3, Q4, Q6, Q7, Q8, Q11 or the like can be referred to. As a further preferable embodiment, cases where X is substituted at the 2- and 3-positions or at the 2-, 3- and 6-positions can be referred to.
The fused heterocyclic dicarboxylic acid diamide derivatives represented by general formula (I) can be produced, for example, according to the production process schematically shown below.